Sulfuric Acid → 6-Bromo-3,4-dihydro-2H-isoquinolin-1-one

HRID 2080763Notes

Reaction equation

HRID 2080763 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.S(=O)(=O)(O)O.[N-:17]=[N+]=[N-].[Na+].C(OCC)(=O)C>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:17][CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 5206955-Bromo-1-indanone

Product 1

HCID 218654506-Bromo-3,4-dihydro-2H-isoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In benzene (71 ml), 5-bromoindanone (5.47 g) was suspended. The solution was added with concentrated sulfuric acid (14 ml) and the whole was vigorously stirred. Then, the solution was gradually added with sodium azide (2.52 g), followed by stirring at room temperature for 30 minutes. The resultant was added with ethyl acetate, washed with water and a saturated saline solution, and dried with magnesium sulfate. The solvent was distilled off.

Workup

  1. stirringby stirring at room temperature for 30 minutes
  2. washwashed with water
  3. dry with materiala saturated saline solution, and dried with magnesium sulfate
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-ef348f3eb0734fc7a50806925f8384db
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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